Shortening treatment



Patented Apr. 1, 1941 2,236,) SHORTENING TREATMENT Donald P. Grettie, Chicago, Ill.

' No Drawing. Application August 12, me.

Serial No. 05,531

2 Claims.

This invention relates to an improved process of treating edible fats and oils.

One of the objects of 'the invention is to provide a method for stabilizing against rancidity edible fats and oils such as lard, beei' iat, hy-

drogenated cottonseed oil, and other vegetable,

and animal fats and oils and mixtures thereof.

Another object of the invention is to provide as an article of commerce, an improved shortening product stabilized against rancidity.

Another object of the invention is to provide an antioxidant for fats and oils'which will 'retard the onset of rancidity and will issue a negative Kreis test during a relatively long induction period.

For the purpose of illustration, but not by way of limitation, the invention is hereinafter described as practiced with lard.

The present invention is based upon the discovery that the tendency of fats and oils to become rancid and to develop a positive Kreis test can be retarded by treatment with hydroxy monobasic aliphaticacids. This invention permits the stabilizing of fats and oils against rancidity without in any way affecting the characteristic flavor oi the shortening treated.

Divers substances have been proposed from time to time as antioxidants for fats and oils, including aromatic acids and such polybasic acids as citric acid.

The present invention is particularly directed to certain of the hydroxy monobasic aliphatic acids, namely, those hydroxy monobasic aliphatic acids which have a hydroxyl radical relatively near the carboxyl end of the molecule as in the alpha or beta position.

Examples of hydroxy monobasic aliphatic acids which may be employed in carrying out the present invention are set out below:

Hudroxy acetic acid CH2OH.COOH Glycolic acid Hudromy proprianic acids Lactic acid CHsCHOHLCOOH Hydrocryuc acid cmoncrroncoorr--. Glyceric acid- Hydroay butyric acid:

CHaCI-I2CHOH.COOH Hydroxy butyric acid CI-Ia(CHOH)zCOOH Dihydroxy butyric acid CH2OH(CHOH) zCOOH- Trihydroxy butyric acid Hydromu valeric acids CHa(CH 2):CHO H.COOI-I- Hydroxy valeric acid CI-IaCHrJCHOH) zCOOH... Dihydroxy valeric acid Hudrozu caprotc acids CHa(CH:):CHOH.COOH- Hydroxy caproic acid 5 cnucrmncnorrncoonu Dihydroxy caproic acid CHaCH2(CI-IOH) 30001-1"--. Trihydroxy caproic acid CHMCHOHMCOOH Quadhydroxy caproic acid Hudroxy heptylic acids crmcrmicnomcoonuu Hydroxy heptylic acid Dihydroxy heptylic acid CH3 (CHa)z(CHOH) 3000K..- Trihydroxy hep- CH3(CH3) 3(CHOH) :C'OOH tylic a'cid CI-IaCI'Iz(CHOH)4COOH Quadhvdroxy heptylic acid CHa(CHOH)cCOOH Penthydroxy heptylic acid Hydroxu cabrulic acids CH3 (CH2) sCHOI-ISOOI-LL- Hydroxy acid caprylic CH3(CH2) 4(CHOH) 26003 CH3(CII2)2(CHOH)4COOH-- Quadhydroxy cap ylic acid CHaCHz(CHOH)sCOOH Penthydroxy caprylic acid CHZ-KCHOHMCOOH Hexhydroxy caprylic acid Hudroaw comic-acids CHa(CI-I2)4(CHOH)4COOH-- Quadhydroxy capric acid CH:(CH:) :(CHOH) sCOOH Penthydroxycapric acid CH: (CI-1:):(CHOH) QCOOHL; Hexliiydroxy capric ac d cmcmwnorr) 100011"--. Septhydroxy capric acid 1 CE1(CHOH)ICH. Octhydroxy capric v acid 5 cnucmncnoncoornm Hydroxy capric acid CHa(CH2)c(CHOH) 200011.- Dihydroxy capric acid CH3(CH2) 5(CHOH)=COOH Trihydroxy capric acid 2 a r 9,986,500 v H Hudroxu lauricacldc I: i v cmwamcnoncoom-" mdroxy lauric acid cnucmnwnonncoonu Dih ydroxy lauric 5 Mould 4 on on crmcmnwnom 300011-. Trihydroxy lauric A acid H- -OOOH cmwmmcnomicoo Quadhydroxy lau- 1'10 v e I cmwmnwnomscoorrn Penthydroxy laum m- H H OH cmwmmcnomecoonu Hexhydroxy laurlc H-i-i-i-coon acid CHa(CH2)a(CHOH)1COOH septhydroxy lauric add Hydroxy butyric acid CH3(CH2)2(CHOH)8COOH. Octhydroxy lauric n on on H-c-c- -coon CHaCI-I2(CHOH)9COOH----. Nonhydroxy lauric I acid CH3(CHOH)10COOH ne i iyaroxy lauric Dihydroxy butyrioacid n n n on Hydroxzl mzlris'tic acids H-i-i-i-i-COOH CHa(CI-I2) 11CHOH.COOH Hydroxy myristic acid Bydroxy valcrlc acid CH:(CH2)10(CHOH)2COOH- Dlhgliiiroxy myristic H H OH on cmcmnwnomacoonn Trihydroxy myrisi'i'i" tic acid CHa(CHa)a(CHOH)-;COOH.. Quadhydrouw my- Dihydroxy veleric acid add n n n n on CH3(CH2)1(CHOH)5COOH-- Pentltiiydroxy my- H a (l; A: 5 C

' rls 0 acid cnncmnwnonncooriu Hexhydroxy myris- 1k 1k ticl acid CH:(CH:)5(CHOH)1COOH Septhydrom' myristic acid H H H 0H 0H crmcnnucnonncoom- Octhydroxy myrisni-i i i-cooe m cm a l l l l CHMCHQMCHOH) oCOOH..- Nonhydr xy ti acid Dihydroxy caproio Mid CHa(CH2)z(CHOH)ioCOOI-I m i ydgf y myris- H ii iii it in tea -----ccon CHaCI-I2(CHOE)11COOH Undhydroxy myristic acid 1k 1]; A 1k CH3(CHOH) 12COOH Didecylichydroxy v Hydroxy heptylic acid myristic acid H H B H 0H 0H Examples of monobasic sugar acids which may Alb-$43005 be employed in carrying out the present inven- H L H tion are set out below. Dmydmy heptync 8cm 1- Pentose Sugar acld H H H H H H OH 2. Hexose sugar acid--- CH2OH(CHOH) ACOOH l J A a J 11 0 -c0on In the foregoing examples of the hydroxy a A 1 2 t a monobasic aliphatic acids only the foundation formula is given in each instance. The present Hydroxy caprylic acid invention is not directed to all forms of each of H H H H H OH on these acids, out only to those forms in which a e (E 22 J: hydroxyl radical occurs in the carbon chain near 3 I the carboxyl end of the molecule. 1 H H H I have found in practice that the invention may be effectively carried out with hydroxy Dihydmy Pryncacm monobasic aliphatic acids having a hydroxyl H H H H H H H OH radical in the alpha or the beta position, or both. H A J j a l l l J For convenience in illustrating the invention the "l 11k" "COOK constitutional formula is given for the alpha 1!! I i 1 {I 2 I hydroxy and the alpha beta dihydroxy form 01 each acid where such forms occur. mm am on nnnnnn-nonon i-i-i-i-ii-i-ti 1 0 acid Dihydroxy ceprlc acid Hydroxyiauricacid H H H H H 0H 0H H- l iiiili'l Jam. llillilllll l Dihydroxy myristic acid It will be understood that other forms of the acids in question than those given may be employed, as will be clear to any chemist skilled in the art, for example, any of the dihydroxy butyric acids are effective whereas in the case of dihydroxy myristic acids th0se forms in which the hydroxyl radical closest to the carboxyl end of the molecule is not closer than the gamma position will be found ineffective, but if there is a hydroxyl radical in either alpha or beta position, the position of the other hydroxyl radical is unimportant and it may occur in the gamma, delta, epsilon, zeta, eta, theta, iota, kappa, lambda or mu position.

The theory which has been herebefore enunciated may be readily applied to such theoretical acids as hydroxy nonyllic acid, hydroxy undecylic acid, hydroxy tridecylic acid and hydroxy quindecylic acid.

By way of illustration I will describe the applic'ation of the invention with select hydroxy monobasic aliphatic acids in the stabilization of lard; I have found in practice that effective stabilization may be secured by the addition of not more than .001 per cent to .05 per cent lactic acid, glycolic acid or gluconic acid to lard. It will be understood, of course, that some stabilization is secured with smaller amounts and that the effect is progressive as the amount is increased although the addition 01' larger amounts gives little apparent increase in stabilizing eflect.

Table A 1. Lard (unstabilizcd).

2. lard containing .01 per cent lactic acid.

3. Lard containing .1 per cent gluconic acid. 4. Lard containing .01 per cent glycolic acid.

Milliequivalents of peroxide oxygen per kilo of fat Hours incubation at 70 C.

snow:

1 Rancid.

1 Faintly rancid.

The stability as determined by the accelerated active oxygen (peroxide keeping test) is as follows:

' Hours Lard 2 Lard containing .01 per cent lactic acid 3 Lard containing .01 per cent glycolic acid 3 Lard containing .01 per cent gluconic acid 4 It will be seen from the foregoing data that lactic, glycolic and gluconic acids have a positive stabilizing effect on lard.

Although lard has been discussed by way of illustration in describing this invention, it will be understood that the invention is not limited to lard but comprehends edible vegetable and anicomprises adding thereto and incorporating therewith from .001 per cent to .05 per cent of lactic acid.

2. As an article of commerce, shortening stabilized against rancidity containing .001 per cent to .05 per cent of lactic acid.

DONALD P. GRE'I'IIE. 

